This invention relates to certain compounds in which a carbon atom of a pyrrolidine or piperidine ring is bonded directly or through a methylene group to the N' nitrogen of an N-phenyl-substituted urea, and their pharmaceutically acceptable salts. The phenyl group of these compounds is substituted by one to three 1,1-dihydroperfluoroalkoxy substituents. The compounds and their pharmaceutically acceptable salts are active as antiarrhythmic agents. The invention also relates to certain novel intermediates and to processes useful to prepare the compounds.
No urea derivatives structurally analogous to the compounds of this invention are known in the art. Local anesthetic activity has been reported by Koelzer and Wehr, Arzneim. Forsch., 8, 664 (1958) for N-(alkylamino)-N' -phenylureas wherein the phenyl ring is substituted by halogen or lower alkyl.
Esters of benzoic acid substituted on the aromatic ring by 1,1-dihydroperfluoroalkoxy substituents are described in U.S. Pat. No. 3,655,728. Certain amides of benzoic acid substituted on the aromatic ring by 1,1-dihydroperfluoroalkoxy substituents are described in U.S. Pat. No. 3,719,687. Other amides of benzoic acid substituted on the aromatic ring by 1,1-dihydroperfluoroalkoxy substituents are described in U.S. Pat. No. 3,900,481.